EP1752434A1 - Procédé amélioré et réacteur pour la préparation d'alpha-oléfines - Google Patents
Procédé amélioré et réacteur pour la préparation d'alpha-oléfines Download PDFInfo
- Publication number
- EP1752434A1 EP1752434A1 EP05017341A EP05017341A EP1752434A1 EP 1752434 A1 EP1752434 A1 EP 1752434A1 EP 05017341 A EP05017341 A EP 05017341A EP 05017341 A EP05017341 A EP 05017341A EP 1752434 A1 EP1752434 A1 EP 1752434A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reactor
- mixing device
- component
- olefins
- ethylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000004711 α-olefin Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000005977 Ethylene Substances 0.000 claims abstract description 18
- 238000006384 oligomerization reaction Methods 0.000 claims abstract description 17
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 230000003068 static effect Effects 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical group CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 3
- 238000011021 bench scale process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/10—Chlorides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
Definitions
- the present invention relates to a method for the preparation of linear alpha-olefins by oligomerization of ethylene in a reactor in the presence of an organic solvent and a homogenous catalyst consisting of a zirconium component and an aluminum component, and a reactor system therefore.
- DE 43 38 414 C1 discloses a method which is carried out in an empty tubular reactor having inlets and outlets for ethylene, oligomerization products and solvent-catalyst mixture.
- the catalytic components are dissolved in the solvent and are introduced into the reactor at a pressure of 31 bar and at a temperature of 40°C.
- a pressure of 31 bar an oligomerization reaction can already take place which may result in plugging of pipes for delivering the catalyst-solvent mixture.
- This object is achieved by a method characterized in that the zirconium component and the aluminum component are pre-mixed in a pre-mixing device, prior to introduction into the reactor, at a temperature range of about 20°C to about 100°C and with a residence time in the pre-mixing device of maximum 75 hours.
- the pre-mixing is carried out continuously in a separate vessel, static mixer, continuously stirred tank or batchwise.
- the solvent is toluene.
- the organoaluminum component is Al(C 2 H 5 ) 3 , Al 2 Cl 3 (C 2 H 5 ) 3 or AlCl(C 2 H 5 ) 2 or mixtures thereof.
- the pre-mixing device is maintained under ethylene pressure of less than 5 bar, preferably under atmospheric pressure.
- pre-mixing is carried out preferably at a temperature of about 50-70°C and with a residence time in the pre-mixing device of about 15 to about 120 minutes, preferably about 30 to about 60 minutes.
- a reactor system for the preparation of linear alpha-olefins by oligomerization of ethylene comprising a reactor and a pre-mixing device connected thereto to pre-mix catalytic components in a solvent, prior to introduction into the reactor.
- the inventive method overcomes the drawbacks of the prior art. Especially, an improved productivity of the oligomerization reactor is obtained, as the preformation of the catalyst is done outside of the reactor. Further, an improved homogeneity of the liquid reaction phase is obtained. Further, start-up and operation of the method is simplified, since the catalyst ratio cannot become wrong within the oligomerization reactor. Also the reactor stability is improved, since a reactor runaway due to over-dosing of one catalyst component is avoided.
- the oligomerization is carried out in an oligomerization reactor 1 having an inlet 2 for introduction of ethylene into the reactor 1, an inlet 3 for introducing a solvent-catalyst mixture, an outlet 4 for removing a mixture of ethylene and light alpha-olefins, and an outlet 5 for removing a liquid mixture consisting of solvent, catalyst, dissolved ethylene and linear alpha-olefins.
- the inlet 3 is fed with the solvent-catalyst mixture from a pre-mixing device 6 having two inlet-lines 7, 8 for separately introducing the catalyst components (zirconium component and aluminum component) into the pre-mixing device 6.
- the rate and amount of each catalyst component may be conveniently controlled.
- the pre-mixing device 6 may be a separate vessel, a static mixer or a continuously stirred tank.
- the pre-mixing may be carried out continuously or batchwise. Further, the pre-mixing preferably performed at a temperature of about 60°C, wherein the catalytic components have a preferred residence time in the pre-mixing device 6 of about 30 to about 60 minutes.
- the catalytic components fed into the pre-mixing device are dissolved in the solvent, preferably toluene.
- the pre-mixing device is maintained under an ethylene pressure of less than 5 bar to avoid an oligomerization reaction therein.
- All materials used for the catalyst were prepared and handled in a glass box filled with nitrogen with less than 1 ppm oxygen and water.
- the catalyst was pre-mixed in a 250 ml round bottom glass flask in a glove box and was stored therein at 20°C from 18-72 hours and then charged into a 2-liter bench scale reactor under nitrogen, whereupon an oligomerization was started at a temperature of 80°C and at an ethylene pressure of 30 bar.
- fresh catalyst was prepared in a glove box at 20°C and then the catalyst was charged into a 2 liter bench scale reactor maintaining the reactor temperature between 40°C-60°C for 15-120 minutes. Ethylene was introduced into the reactor after the predetermined premixing time until the desired 30 bar pressure was obtained and the reaction temperature was held at 80°C.
- the catalytic activity was calculated as the amount of ethylene consumed in one hour. After one hour, the reaction was stopped. A sample of liquid LAO product was collected in a glass veil and analyzed by gas chromatography (GC) at room temperature.
- GC gas chromatography
- Example 1 of table 1 is an oligomerization run utilizing a standard LAO catalyst without premixing of the catalytic components.
- the data of examples 2 to 5 indicate that catalyst aging with time (18-72 hours) has increased the catalyst activity, LAO yield and selectivity. It was found that the pre-mixed catalyst was quite stable during this period as compared to standard fresh catalyst.
- example 10 of table 1 the catalyst was pre-mixed and stored for 30 hours at 20°C in the glove box and was then charged into the reactor, whereupon the reactor temperature was maintained at 50°C for 30 minutes. After that by introduction of ethylene the reaction was started to be conducted at a temperature of 80°C.
- the results of example 10 show that the catalyst activity, LAO yield and selectivity were slightly increased.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05017341A EP1752434A1 (fr) | 2005-08-10 | 2005-08-10 | Procédé amélioré et réacteur pour la préparation d'alpha-oléfines |
| CA002617634A CA2617634A1 (fr) | 2005-08-10 | 2006-06-13 | Procede ameliore pour la preparation d'alpha-olefines lineaires et systeme de reacteur pour celui-ci |
| BRPI0615154-0A BRPI0615154A2 (pt) | 2005-08-10 | 2006-06-13 | método aperfeiçoado para a preparação de alfa-olefinas lineares e sistema de reator para isso |
| PCT/EP2006/005640 WO2007016991A1 (fr) | 2005-08-10 | 2006-06-13 | Procede ameliore pour la preparation d'alpha-olefines lineaires et systeme de reacteur pour celui-ci |
| JP2008525401A JP2009504578A (ja) | 2005-08-10 | 2006-06-13 | 線状アルファオレフィンの調製方法およびそのための反応装置系 |
| RU2008108813/04A RU2008108813A (ru) | 2005-08-10 | 2006-06-13 | Улучшенный способ получения линейных альфа-олефинов и реакторная система для его осуществления |
| KR1020087003851A KR20080037031A (ko) | 2005-08-10 | 2006-06-13 | 개선된 선형 알파-올레핀의 제조 방법 및 이를 위한 반응기시스템 |
| CNA2006800288385A CN101238085A (zh) | 2005-08-10 | 2006-06-13 | 用于制备线型α-烯烃的改进方法和用于该方法的反应器系统 |
| TW095121751A TW200800849A (en) | 2005-08-10 | 2006-06-16 | Improved method for preparation of linear alpha-olefins and reactor system therefore |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05017341A EP1752434A1 (fr) | 2005-08-10 | 2005-08-10 | Procédé amélioré et réacteur pour la préparation d'alpha-oléfines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1752434A1 true EP1752434A1 (fr) | 2007-02-14 |
Family
ID=35531785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05017341A Withdrawn EP1752434A1 (fr) | 2005-08-10 | 2005-08-10 | Procédé amélioré et réacteur pour la préparation d'alpha-oléfines |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1752434A1 (fr) |
| JP (1) | JP2009504578A (fr) |
| KR (1) | KR20080037031A (fr) |
| CN (1) | CN101238085A (fr) |
| BR (1) | BRPI0615154A2 (fr) |
| CA (1) | CA2617634A1 (fr) |
| RU (1) | RU2008108813A (fr) |
| TW (1) | TW200800849A (fr) |
| WO (1) | WO2007016991A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10513473B2 (en) | 2015-09-18 | 2019-12-24 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| US10519077B2 (en) | 2015-09-18 | 2019-12-31 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| WO2022250885A2 (fr) | 2021-05-26 | 2022-12-01 | Chevron Phillips Chemical Company Lp | Procédés d'oligomérisation des éthylènes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4338414C1 (de) * | 1993-11-10 | 1995-03-16 | Linde Ag | Verfahren zur Herstellung linearer Olefine |
| US20040010098A1 (en) * | 2000-12-05 | 2004-01-15 | Georg Groos | Device for feeding reactor initiators |
-
2005
- 2005-08-10 EP EP05017341A patent/EP1752434A1/fr not_active Withdrawn
-
2006
- 2006-06-13 KR KR1020087003851A patent/KR20080037031A/ko not_active Withdrawn
- 2006-06-13 WO PCT/EP2006/005640 patent/WO2007016991A1/fr active Application Filing
- 2006-06-13 JP JP2008525401A patent/JP2009504578A/ja not_active Withdrawn
- 2006-06-13 CA CA002617634A patent/CA2617634A1/fr not_active Abandoned
- 2006-06-13 CN CNA2006800288385A patent/CN101238085A/zh active Pending
- 2006-06-13 BR BRPI0615154-0A patent/BRPI0615154A2/pt not_active Application Discontinuation
- 2006-06-13 RU RU2008108813/04A patent/RU2008108813A/ru not_active Application Discontinuation
- 2006-06-16 TW TW095121751A patent/TW200800849A/zh unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4338414C1 (de) * | 1993-11-10 | 1995-03-16 | Linde Ag | Verfahren zur Herstellung linearer Olefine |
| US20040010098A1 (en) * | 2000-12-05 | 2004-01-15 | Georg Groos | Device for feeding reactor initiators |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10513473B2 (en) | 2015-09-18 | 2019-12-24 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| US10519077B2 (en) | 2015-09-18 | 2019-12-31 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| US10927054B2 (en) | 2015-09-18 | 2021-02-23 | Chevron Phillips Chemical Company, Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| US11623900B2 (en) | 2015-09-18 | 2023-04-11 | Chevron Phillips Chemical Company, Lp | Ethylene oligomerization/trimerization/tetramerization reactor |
| WO2022250885A2 (fr) | 2021-05-26 | 2022-12-01 | Chevron Phillips Chemical Company Lp | Procédés d'oligomérisation des éthylènes |
| US11667590B2 (en) | 2021-05-26 | 2023-06-06 | Chevron Phillips Chemical Company, Lp | Ethylene oligomerization processes |
| US11873264B2 (en) | 2021-05-26 | 2024-01-16 | Chevron Phillips Chemical Company Lp | Ethylene oligomerization processes |
| EP4545620A2 (fr) | 2021-05-26 | 2025-04-30 | Chevron Phillips Chemical Company LP | Procédés d'oligomérisation d'éthylène |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101238085A (zh) | 2008-08-06 |
| BRPI0615154A2 (pt) | 2011-05-03 |
| JP2009504578A (ja) | 2009-02-05 |
| RU2008108813A (ru) | 2009-09-20 |
| WO2007016991A1 (fr) | 2007-02-15 |
| TW200800849A (en) | 2008-01-01 |
| CA2617634A1 (fr) | 2007-02-15 |
| KR20080037031A (ko) | 2008-04-29 |
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Owner name: SAUDI BASIC INDUSTRIES CORPORATION Owner name: LINDE AG |
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